Stable arseno-benzene derivatives and process of making same



Patented Urt. lU, if.

wrLHEm/i noun, or FnAn ronr-on-Tnn-iivmm, AND ARTHUR BINZ, orxnnnnm, GERMANY, AS$IGNOB$ T0 FARBWERKE VOEM-. MEIS'IER LUCIUS 8. BRUNZENG'Z 0F HOECHST-ONTHE-MAII\T, GERMANY, A oonronnrron or GERMANY.

STABLE ARSENO-BENZ ENE DERIVATIVES AND PROCESS 01E!" MAKING SAME.

Itl'o Drawing.

To all whom it may concern:

Be it known that we, W. KOLLE, and ARTHUR BINZ, citizens of Germany, residing at Frankfort-on-the-Main and Berlin, Germany, respectively, have invented. certain new and useful Improvements in. Stable Arseno-Benzene Derivatives and Process of Making Same, of which the following is a specification.

As is known, the diaminodioxyarsenobenzone and its derivatives have the disadvantage, that they can be used only in quite freshly prepared solutions, because their solutions very quickly decompose and consequently their toxicity increases while their spirillocide action diminishes.

Now we have made the surprising discovery that by mixing aqueous solutions o'li sulphoxylate of 3.3 -diamino-4.4-dioxyarsenobenzene and the sodium salt of the silver compound of 3.3-diamino-a At-dioxyarsenobenzene, a new substance is obtained which, unlike the components of which said substance consists, keeps well for many hours in aqueous solution as well as in the air, without formation of any precipitate or increase of toxicity or any loss of its therapeutical efliciency. This new solution is therefore of great practical value and constitutes an important advance from a technical and therapeutical point of view. When there is substituted for the silver compound of the sodium salt of the diaminodioxyarsenobenzene the sodium salt itself, the reaction ocours in like manner, as is evident from the fact that, when introducing carbon dioxide into the reaction-mixture, there is no precipitation of dioxydiaminoarsenobenzene.

The production of stable compounds is not limited to the above described special cases of combinations of certain arsenobenzene derivatives with the methylene sulfoxylate of 3.3-diamino-4.4E-dioxyarsenobenzene, but there are quite generally obtained products of particular stability by combining sulfoxylates of the arsenobenzenes with other arsenobenzene derivatives. Moreover we have found that the increased stability is Application filed October 20, 1921. Serial No. 509,169.

not limited to the combination with sulfoxylates of the arsenobenzenes, but that quite an analogous effect is produced by the admixture of carbamates of the arsenobenzenes. Also such combinations as contain carbamates and sulfoxylates together, give the same result.

The combination of the several components may be effected either by making the substances themselves or by combiningsolutions of them. i

The following examples illustrate our invention:

l. 3 gr. of sulphoxylate of 3.3 diamino- 4c.t-dioxyarsenobenzenef'and 3 gr. of the silver compound of the sodium salt of 3.3 diamino- LA dioxyarsenobenzene are mixed in a powdered form and then stirred with 5 corn. of water. When carbon dioxide is in troduced into the solution thus obtained, there is no preoipitationwhereas such precipitation would immediately occur in presence of any unaltered silver compound of the sodium salt. Furthermore, when the solution is allowed to stand for some time it gives, on addition of common salt, no precipitate, a fact which also proves that the silver compound of the sodium salt of 3.3- diamino- L/i' dioxyarsenobenzene is no longer present as such, but hasentered into reaction, for a solution of the silver compound precipitates on addition of sodium chloride if it has stood for some time.

2. 3 gr. of sulphoxylate of 3.3-diamino- 4.4-dioxyarsenobenzene are dissolved in 3 com. of water and likewise 3 gr. of the sodium salt of 3.3-diam'ino-4;.4c'-dioxyarsenobenzene in 3 com. of water. Any precipitate which may be formed is redissolved by adding a small quantity of caustic soda lye. When the two solutions have been mixed, there is no separation of dioxydiamino arsenobenzene on introducing carbon dioxide, a fact which proves that the sodium salt of the 3.3-diamino 4.4 dioxyarsenobenzene is nolonger present as such, but has combined with the sulfoxylate of the diaminodioxyarsenobenzene.

1. Component in 2. Component in Properties of the a e e 10 com. of water. 10 com. of water. mixture.

mples.

I. 1 gr. of i-amino- 1 gr. of i-amino- W h e n diluted arsenophen ylarsenophe nylwith water dimethyl-pydirneth yl p ythere is no prerazolon carbarazolon metheipitate. mate; when diylene-sulioxylluted with waate. ter there will be a precipitate after a few minutes. v

II. The same as in 1gr.oI3.3-diami- Who 11 diluting Example I. no 4-dioxyt h e solution arsenobe nzenewith water and methylene-sulkeeping it in ioxylate. T h e storage, it is solution, when stable not oxikept in storage dizable and not i s decompostoxic. able, oxidizable and toxic.

III. 0.5 gr. of 4-amino- 1 gr. of 3.3 diami- When diluting arsenophenylno-4.4'-dioxyt h 6 solution dimethyl-pyraarsenobenzenewith water and zolon-carb amethylene-sulkeeping it in mate; when diioxylate; the sostorage it is luted with walution w h e n stable, little ter there will be kept in storage, oxidizable and a precipitate is decomposthere is no esaiter a few minable, oxidizable sential increase utes. and toxic. of the toxicity. IV. 0.5 gr. of dimethyl- 1gr.oi3.3-diamino- When kept in hex am inoar 4.4 dioxyarsenostorage it is stasenobenzene. benzene methyble, not oxidiz- This assumes lene sull'oxylate; able, does not when exposed to the s ol uti on, turn red when i the air immewhen kept in exposed to the diately a red storage, is dethe air and is color and is composable, oxnot toxic. toxic when kept id i z a b l e and in storage. toxic.

V. 1 r. of dimethyl- 10 corn. of the mix- Does not turn red ex aminoarture of Example when exposed senobenzene I. w to theair;andis turns immednot toxic when diatelyred when kept in storage. exposed to the air and is toxic when kept in storage.

VI. The same asin Ex- 1 gr. ofthe sodium Is stable when diample III. salt of 4-aminol u t e d w i t h arseno henylwater.

dimet y l -pyrazolonglycine.

Having now described our invention, what we claim is:

1. The process of making arsenical preparations which are stable in solution, which comprises mixing water-soluble arsenobenzene compounds represented by the formula RNHR in which R stands for any arsenobenzene residue and R stands for sulfoxylate or carbamate residue with other watersoluble arsenobenzene compounds.

2. The process of making arsenical preparations which are stable in solution which comprises combining in solution a watcrsoluble arsenobenzene compound represented by the formula RNHR in which R stands for any arsenobenzene residue and R stands for sulfoxylate or carbamate residue with other water soluble arsenobenzene compounds.

3. As new products, bodies containing arsenobenzene compounds represented by the formula RNHR in which R stands for any arsenobenzene residue and R stands for sulfoxylate or carbamate residue in combination with other arsenobenzene compounds.

4. As new products, bodies containing arsenobenzene compounds represented by the formula R.NH.R in which R stands for any arsenobenzene residue and R stands for sulfoxylate or carbamate residue chemically combined with other arsenobenzene compounds.

In testimony whereof, we aflix our signatures.

WILHELM KOLLE. ARTHUR BINZ. 

